5-benzyloxy-1-hydroxy-3-hydroxy-2-methyl-α-D-arabinose | 1583259-79-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-benzyloxy-1-hydroxy-3-hydroxy-2-methyl-α-D-arabinose
• CAS: 1583259-79-3
• 化学式: C₁₃H₁₈O₄
• 分子量: 238.284
• InChiKey: DZZIODQUHFQZCU-RYDUCSDGSA-N

物化性质

• 沸点：
  413.7±45.0 °C(Predicted)
• 密度：
  1.201±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.92
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  58.92
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  (3S,4R)-isopropyl 5-(benzyloxy)-3-hydroxy-2-methyl-4-(2,2,6,6-tetramethylpiperidin-1-yloxy)pentanoate 在 水 、 二异丁基氢化铝 、 三氟乙酸 、 锌 作用下， 以 甲苯 为溶剂， 反应 18.0h， 生成 5-benzyloxy-1-hydroxy-3-hydroxy-2-methyl-β-D-arabinose 、 5-benzyloxy-1-hydroxy-3-hydroxy-2-methyl-α-D-arabinose
  参考文献：
  名称：

  A General and Enantioselective Approach to Pentoses: A Rapid Synthesis of PSI-6130, the Nucleoside Core of Sofosbuvir

  摘要：

  An efficient route towards biologically relevant pentose derivatives is described. The de novo synthetic strategy features an enantioselective alpha-oxidation reaction enabled by a chiral amine in conjunction with copper(II) catalysis. A subsequent Mukaiyama aldol coupling allows for the incorporation of a wide array of modular two-carbon fragments. Lactone intermediates accessed via this route provide a useful platform for elaboration, as demonstrated by the preparation of a variety of C-nucleosides and fluorinated pentoses. Finally, this work has facilitated expedient syntheses of pharmaceutically active compounds currently in clinical use.

  DOI：

  10.1021/ja502205q